Organosilicon oils



Patented July 22, 1952 UNITED STATES PATENT OFFICE ORGAN OSILICON OILS Charles A. Burkhard, Alplaus, N. Y., assignor to General Electric Company, a corporation of New York No Drawing. Application May 21, 1951, Serial No. 227,505

'3 Claims.

The present invention relates to organosilicon oils comprising chemical compounds of silicon, oxygen, sulfur, carbon and hydrogen. It is more specifically concerned with oily compositions comprising organosilicon compounds of the unit structure.

wherein n is a number from to 10, preferably 0 or 1, m is an integer equal to at least 2, and preferably from 2 to 6, y is'equal to 2 or 3, and m is an integer equal to at least 1. It will be noted that the compounds are particularly character- 'ized by the presence in the unit structure of the wherein m is an integer equal to at least 2, preferablyZ to 6, and (2) a dialkenyl silane or siloxane of the formula wherein R represents a terminally unsaturated alkenyl radical, e. g., a vinyl or allyl radical and n is a number from 0 to 10, preferably 0 or 1. A representative compound of (1) when m is equal to 2 is ethylene bisthioglycolate prepared from thioglycolic acid and ethylene glycol and representative compounds of (2) are diallyldimethylsilane, divinyldimethylsilane, sym diallyltetramethyldisiloxane (n=1) and sym divinylhexamethyltrisiloxane (n=2).

The reaction appears to proceed exclusively by the addition of th S--H bond to the alkenyl radical as no sulfur is lost during the reaction and the products do not react with standard iodine solution indicating that the S-H bond has disappeared.

The oily products of the present invention can be used as lubricating oils, hydraulic fluids and as lubricity additives for petroleum oils or other organosilicon oils. They may also be employed as plasticizers for organo silicon resins and elastomers and polyvinyl halide resins.

In order that those skilled in the art better may understand how the present invention may be carried into effect, the following illustrative examples are given:

Example 1.--Ethylene bisthioglycolate was mixed with an equimolar quantity of diallyldimethylsilane and a small amount of benzoyl peroxide added to initiate the reaction. After shaking, the mixture was allowed to stand for a few hours. The product was a viscous oil having the unit structure where :0 equals at least 1. Analysis for sulfur gave 18.65% as compared with a calculated content of 18.29.

Example 2.The process of Example 1 was repeated employing diallyltetramethyldisiloxane,

[(CH2=CH CH2) (CH3) zsnzo in place of the diallyldimethylsilane. The product was a high molecular weight oil of about the same viscosity as that of Example 1 and having the unit structure [-(CHz)3Si(CH3)2OSi(CH3)2(CI-I2)3 SCI-12002 (CH2) 2O2CC'H2S] :c

and a sulfur analysisof 10.05, calculated 10.6.

Other compounds or oils of the present invention are prepared by reacting the higher divinyl or diallyl polymethyl siloxanes with either ethylene bisthioglycolate or other diesters of thioglycolic acid and a higher dihydric alcohol such as trimethylene glycol, etc.

What I claim as new and desire to secure by Letters Patent of the United States is:

1. An organosilicon oil comprising the unit structur [(CH2) ySi (CI-I3) 2{OSi(CH3) 2} I wherein rn is a number from 0 to 10, m is an integer equal to at least 2, y is one of the integers,

where :0 equals at least 1.

3. An organosilicon oil comprising the unit structure and a: is an integer equal to at least 1.

CHARLES A. BURKHARD.

No references cited. 

1. AN ORGANOSILICON OIL COMPRISING THE UNIT STRUCTURE 